Water → 2-bromo-4-(3-fluorophenyl)Thiazole
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][S:10][C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1.[BrH:14].C(O)(=O)C.O>C(O)(=O)C>[Br:14][C:11]1[S:10][CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[N:12]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To a solution of 2-(3-fluorophenyl)-2-oxoethyl thiocyanate (1.76 g, 9.02 mmol) in acetic acid (15 ml) was added a 25% hydrogen bromide/acetic acid solution (15 ml), and the mixture was stirred at 130° C. for 2 hours and at room temperature for 2 hours. Water was poured into the reaction solution, and the mixture was extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=9:1) to give the desired product (2.31 g, 99.0%) as an oil.
Workup
- extractionthe mixture was extracted with chloroform
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=9:1)
Sources & evidence
- ORD record
- ord-a8f9643ce21f46ebbabc2456526aa81e
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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